Sense of "to be victorious" is recorded from c.1300. Breadwinner preserves the sense of "toil" in Old English winnan. Phrase you can't win them all (1954) first attested in Raymond Chandler. Winningest is attested by 1804.

n.

Old English winn "labor, strife, conflict," from the source of win (v.). Modern sense of "a victory in a game or contest" is first attested 1862, from the verb.